钯催化的烯烃链行走异构化反应
Palladium-catalysed alkene chain-running isomerization.
作者信息
Kocen Andrew L, Brookhart Maurice, Daugulis Olafs
机构信息
Department of Chemistry, University of Houston, Houston, TX 77204-5003, USA.
出版信息
Chem Commun (Camb). 2017 Sep 5;53(72):10010-10013. doi: 10.1039/c7cc04953f.
Abstract
We report a method for palladium-catalysed chain-running isomerization of terminal and internal alkenes. Using an air-stable 2,9-dimethylphenanthroline-palladium catalyst in combination with NaBAr promoter, olefins are converted to the most stable double bond isomer at -30 to 20 °C. Silyl enol ethers are readily formed from silylated allylic alcohols. Fluorinated substituents are compatible with the reaction conditions, allowing the synthesis of fluoroenolates. Catalyst loading as low as 0.05% can be employed on a gram scale.
摘要
我们报道了一种用于钯催化的末端烯烃和内烯烃链行走异构化的方法。使用空气稳定的2,9-二甲基菲咯啉-钯催化剂与NaBAr促进剂相结合，烯烃在-30至20°C下转化为最稳定的双键异构体。甲硅烷基烯醇醚可由甲硅烷基化的烯丙醇容易地形成。氟化取代基与反应条件相容，从而能够合成氟代烯醇盐。在克级规模上可采用低至0.05%的催化剂负载量。
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